Hydrogen-bond directionality and symmetry in
[C(O)NH](N)(2)P(O)-based structures: a comparison between X-ray
crystallography data and neutron-normalized values, and
evaluation of reliability

J 2021

Hydrogen-bond directionality and symmetry in [C(O)NH](N)(2)P(O)-based structures: a comparison between X-ray crystallography data and neutron-normalized values, and evaluation of reliability

TAHERZADEH, Maryam, Mehrdad POURAYOUBI, Banafsheh Vahdani ALVIRI, Samad Shoghpour BAYRAQ, Maral ARIANI et. al.

Basic information

Original name

Hydrogen-bond directionality and symmetry in [C(O)NH](N)(2)P(O)-based structures: a comparison between X-ray crystallography data and neutron-normalized values, and evaluation of reliability

Authors

TAHERZADEH, Maryam, Mehrdad POURAYOUBI (guarantor), Banafsheh Vahdani ALVIRI, Samad Shoghpour BAYRAQ, Maral ARIANI, Marek NEČAS (203 Czech Republic, belonging to the institution), Michal DUŠEK, Václav EIGNER, Hadi Amiri RUDBARI, Giuseppe BRUNO, Teresa Mancilla PERCINO, Marco A. LEYVA-RAMÍREZ and Krishnan DAMODARAN

Edition

Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, International Union of Crystallography, 2021, 2052-5206

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10406 Analytical chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 2.684

RIV identification code

RIV/00216224:14310/21:00122973

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1107/S2052520621003371

UT WoS

000661270800012

Keywords in English

phosphoric triamide; X-ray diffraction; neutron normalization; symmetry; Cambridge Structural Database; lone electron pair

Abstract

V originále

For [C(O)NH](N)2P(O)-based structures, the magnitude of the differences in the N—H⋯O, H⋯O=P and H⋯O=C angles has been evaluated when the N—H bond lengths, determined by X-ray diffraction, were compared to the neutron normalized values and the maximum percentage difference was obtained, i.e. about 3% for the angle even if the N—H bond lengths have a difference of about 30% (0.7 Å for the X-ray and 1.03 Å for the neutron-normalized value). The symmetries of the crystals are discussed with respect to the symmetry of the molecules, as well as to the symmetry of hydrogen-bonded motifs, and the role of the most directional hydrogen bond in raising the probability of obtaining centrosymmetric crystal structures is investigated. The work was performed by considering nine new X-ray crystal structures and 204 analogous structures retrieved from the Cambridge Structural Database.

Links

LM2018127, research and development project

Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

TAHERZADEH, Maryam, Mehrdad POURAYOUBI, Banafsheh Vahdani ALVIRI, Samad Shoghpour BAYRAQ, Maral ARIANI, Marek NEČAS, Michal DUŠEK, Václav EIGNER, Hadi Amiri RUDBARI, Giuseppe BRUNO, Teresa Mancilla PERCINO, Marco A. LEYVA-RAMÍREZ and Krishnan DAMODARAN. Hydrogen-bond directionality and symmetry in [C(O)NH](N)(2)P(O)-based structures: a comparison between X-ray crystallography data and neutron-normalized values, and evaluation of reliability. Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials. International Union of Crystallography, 2021, vol. 77, No 3, p. 384-396. ISSN 2052-5206. Available from: https://dx.doi.org/10.1107/S2052520621003371.

@article{1804948,
   author = {Taherzadeh, Maryam and Pourayoubi, Mehrdad and Alviri, Banafsheh Vahdani and Bayraq, Samad Shoghpour and Ariani, Maral and Nečas, Marek and Dušek, Michal and Eigner, Václav and Rudbari, Hadi Amiri and Bruno, Giuseppe and Percino, Teresa Mancilla and LeyvaandRamírez, Marco A. and Damodaran, Krishnan},
   article_number = {3},
   doi = {http://dx.doi.org/10.1107/S2052520621003371},
   keywords = {phosphoric triamide; X-ray diffraction; neutron normalization; symmetry; Cambridge Structural Database; lone electron pair},
   language = {eng},
   issn = {2052-5206},
   journal = {Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials},
   title = {Hydrogen-bond directionality and symmetry in [C(O)NH](N)(2)P(O)-based structures: a comparison between X-ray crystallography data and neutron-normalized values, and evaluation of reliability},
   url = {https://doi.org/10.1107/S2052520621003371},
   volume = {77},
   year = {2021}
}

TY  - JOUR
ID  - 1804948
AU  - Taherzadeh, Maryam - Pourayoubi, Mehrdad - Alviri, Banafsheh Vahdani - Bayraq, Samad Shoghpour - Ariani, Maral - Nečas, Marek - Dušek, Michal - Eigner, Václav - Rudbari, Hadi Amiri - Bruno, Giuseppe - Percino, Teresa Mancilla - Leyva-Ramírez, Marco A. - Damodaran, Krishnan
PY  - 2021
TI  - Hydrogen-bond directionality and symmetry in [C(O)NH](N)(2)P(O)-based structures: a comparison between X-ray crystallography data and neutron-normalized values, and evaluation of reliability
JF  - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
VL  - 77
IS  - 3
SP  - 384-396
EP  - 384-396
PB  - International Union of Crystallography
SN  - 20525206
KW  - phosphoric triamide
KW  - X-ray diffraction
KW  - neutron normalization
KW  - symmetry
KW  - Cambridge Structural Database
KW  - lone electron pair
UR  - https://doi.org/10.1107/S2052520621003371
N2  - For [C(O)NH](N)2P(O)-based structures, the magnitude of the differences in the N—H⋯O, H⋯O=P and H⋯O=C angles has been evaluated when the N—H bond lengths, determined by X-ray diffraction, were compared to the neutron normalized values and the maximum percentage difference was obtained, i.e. about 3% for the angle even if the N—H bond lengths have a difference of about 30% (0.7 Å for the X-ray and 1.03 Å for the neutron-normalized value). The symmetries of the crystals are discussed with respect to the symmetry of the molecules, as well as to the symmetry of hydrogen-bonded motifs, and the role of the most directional hydrogen bond in raising the probability of obtaining centrosymmetric crystal structures is investigated. The work was performed by considering nine new X-ray crystal structures and 204 analogous structures retrieved from the Cambridge Structural Database.
ER  -

TAHERZADEH, Maryam, Mehrdad POURAYOUBI, Banafsheh Vahdani ALVIRI, Samad Shoghpour BAYRAQ, Maral ARIANI, Marek NEČAS, Michal DUŠEK, Václav EIGNER, Hadi Amiri RUDBARI, Giuseppe BRUNO, Teresa Mancilla PERCINO, Marco A. LEYVA-RAMÍREZ and Krishnan DAMODARAN. Hydrogen-bond directionality and symmetry in [C(O)NH](N)(2)P(O)-based structures: a comparison between X-ray crystallography data and neutron-normalized values, and evaluation of reliability. \textit{Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials}. International Union of Crystallography, 2021, vol.~77, No~3, p.~384-396. ISSN~2052-5206. Available from: https://dx.doi.org/10.1107/S2052520621003371.

Detailed Information on Publication Record